Veratrole → 3,4-Dimethoxybenzophenone

HRID 1745348Notes

Reaction equation

CO[C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1OC)[C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)=[O:7].C1(OC)C(=CC=CC=1)OC.[Cl-].[Al+3].[Cl-].[Cl-].C(Cl)(=O)C1C=CC=CC=1>>[CH3:17][O:16][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][C:11]=1[O:14][CH3:15])[C:6]([C:5]1[CH:18]=[CH:19][CH:20]=[CH:3][CH:4]=1)=[O:7]

Participants

Reactant 4

HCID 7043Veratrole

HCID 7412Benzoyl chloride

HCID 223042Bis(3,4-dimethoxyphenyl)methanone

HCID 6451240Aluminum(III) Chloride

Product 1

HCID 2867423,4-Dimethoxybenzophenone

Procedure

3,4-Dimethoxybenzophenone was prepared analogously to 3,4,3′,4′-tetramethoxybenzophenone using veratrole (2 mL, 15 mmol), aluminum chloride (2.2 g, 16.5 mmol) and benzoyl chloride (1.8 mL, 15.5 mmol). The crude mixture was purified by flash column chromatography (silica gel, 3% ethyl acetate/methylene chloride) to yield 3.44 g (93%) of the product as a white solid: mp 99–100° C.; 1H NMR (CDCl3) δ 7.82–7.30 (m, 7H), 6.95–6.85 (m, 1H), 3.96 (s, 3H), 3.94 (s, 3H); 13C NMR (CDCl3) δ 195.5, 153.0, 149.0, 138.2, 131.8, 130.2, 129.6, 128.1, 125.4, 112.1, 109.7, 56.0, 56.0; Anal. Calcd for C15H14O3. Theoretical: C, 74.36; H, 5.82. Found: C, 74.21; H, 6.01.

Workup

customThe crude mixture was purified by flash column chromatography (silica gel, 3% ethyl acetate/methylene chloride)

Sources & evidence

ORD record: ord-aa9f7b090bc247849d2ecf5b25806b54
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07019030B2

Reaction notes

Loading…